The compounds of this invention are highly active as preemergent and/or postemergent herbicides or plant growth regulants. They are especially useful for the control of grasses, broadleaves and sedges with a high degree of rice selectivity.
U.S. Pat. No. 4,397,679 discloses herbicidal sulfonamides of formula ##STR1##
European patent application (EP-A) No. 44,209 discloses, in part, herbicidal sulfonamides of formula ##STR2##
Sourth African patent application No. 83/4956 discloses, in part, herbicidal sulfonamides of formula ##STR3## wherein B and D are independently a single chemical bond, methylene or ethylene group, which can be substituted or unsubstituted; and
R.sub.4 is C(O)R.sub.7 or a functional derivative thereof. PA1 R.sub.4 is H, F, Cl, Br or CH.sub.3 ; and PA1 R.sub.5 is F, Cl, Br, OC(O)R.sub.6, OC(O)CF.sub.3, OH, OCH.sub.2 Ph, OSO.sub.2 R.sub.6, OSO.sub.2 CF.sub.3, OSO.sub.2 C.sub.6 H.sub.5 R.sub.7, S(O).sub.m R.sub.6, OSO.sub.2 N(CH.sub.3).sub.2 or CO.sub.2 R.sub.8. PA1 R.sub.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.14, CONR.sub.12 R.sub.13, NR.sub.12 R.sub.13, SONR.sub.15 R.sub.16, OSO.sub.2 R.sub.17 or COR.sub.18 ; PA1 R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA1 R.sub.3 and R.sub.4, independently of one another, are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 alkoxyalkyl or NR.sub.19 R.sub.20 ; PA1 R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA1 R.sub.10 is hydrogen, halogen or methyl; PA1 R.sub.11 is a radical COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group that is mono- or polysubstituted by substituents selected from the group: cyano, nitro, hydroxyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, etc. PA1 R.sub.18 is H, C.sub.1 -C.sub.4 alkoxy, NR.sub.12 R.sub.13, SO.sub.2 NR.sub.15 R.sub.16 and various other organic radicals. PA1 R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.a and R.sub.b may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 Q is --(CH.sub.2).sub.n -- which may be optionally substituted with 1-3 substituents selected from the group consisting of C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 thioalkyl, halogen, cyano or NO.sub.2 ; PA1 n is 1, 2 or 3; PA1 R.sub.2 is SO.sub.2 NR.sub.4 R.sub.5, NR.sub.4 R.sub.5, SCN, SH or N.sub.3 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.3 alkyl or phenyl; PA1 R.sub.4 and R.sub.5 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; or PA1 R.sub.4 and R.sub.5 may be taken together to form --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 A is ##STR9## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl or N(OCH.sub.3)CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.6, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (c) when R.sub.2 is SO.sub.2 NR.sub.4 R.sub.5, NR.sub.4 R.sub.5 or SH, then n is 2 or 3; and PA1 (d) when J is J.sub.2, then the substituent QR.sub.2 and the sulfonylurea bridge are on adjacent carbon atoms. PA1 1. Compounds of Formula I where A is A-1; J is J-1; and R.sub.2 is SO.sub.2 NR.sub.4 R.sub.5. PA1 2. Compounds of Preferred 1 where R.sub.1 is H, C.sub.1 -C.sub.2 alkyl, F, Cl, Br, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or C.sub.1 -C.sub.2 haloalkoxy. PA1 3. Compounds of Preferred 2 where Q is CH.sub.2 CH.sub.2 or CH.sub.2 CH.sub.2 CH.sub.2. PA1 4. Compounds of Preferred 3 where PA1 5. Compounds of Preferred 4 where Q is CH.sub.2 CH.sub.2 ; and R.sub.4 and R.sub.5 are independently H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl. PA1 6. Compounds of Formula I where J is J-2, J-3 or J-4; and R.sub.2 is SO.sub.2 NR.sub.4 R.sub.5 or NR.sub.4 R.sub.5. PA1 7. Compounds of Preferred 6 where PA1 8. Compounds of Preferred 7 where Q is CH.sub.2 CH.sub.2 ; and R.sub.4 and R.sub.5 are independently H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl. PA1 9. Compounds of Preferred 8 where J is J-2. PA1 10. Compounds of Preferred 8 where J is J-3 or J-4. PA1 11. Compounds of Formula I where R.sub.2 is SH, SCN or N.sub.3. PA1 12. Compounds of Preferred 12 where PA1 13. Compounds of Preferred 13 where J is J-1. PA1 14. Compounds of Preferred 13 where J is J-2. PA1 15. Compounds of Preferred 13 where J is J-3 or J-4. PA1 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N,N-dimethylb enzeneethanesulfonamide, m.p. 152.degree.-156.degree. C.; and PA1 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N,N -dimethylbenzeneethanesulfonamide, m.p. 154.degree.-157.5.degree. C. PA1 R is H or CH.sub.3. PA1 R is H. PA1 R is H; and PA1 A is as previously defined. PA1 R.sub.6 is CH.sub.3 or --C.sub.6 H.sub.4 --4--CH.sub.3 ; and PA1 R.sub.7 is H or C(CH.sub.3).sub.3. PA1 R.sub.2 is SCN, N.sub.3, or NR.sub.4 R.sub.5 ; PA1 R.sub.4 and R.sub.5 are not H; and PA1 M is Na or K. PA1 Q is --(CH.sub.2).sub.n -- which may be optionally substituted with 1-3 substituents selected from the group consisting of C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 thioalkyl, halogen, cyano or NO.sub.2 ; PA1 n is 1 or 2; PA1 R.sub.4 and R.sub.5 are as previously defined; and PA1 R.sub.8 is CH.sub.3 or CH.sub.2 CH.sub.3.
EP-A-106,512 discloses, in part, herbicidal sulfonamides of formula ##STR4## wherein n is 0 or 1;
South African patent application 83/6449 discloses, in part, herbicidal sulfonamides of formula ##STR5## wherein R.sub.3 is a C.sub.2 -C.sub.10 alkenyl group which is substituted by one or more fluorine or bromine atoms or by one or more hydroxyl, cyano, nitro, --(Y).sub.m CO(Z).sub.n R.sub.8, --SO.sub.2 NR.sub.11 R.sub.12, --S(O).sub.P C.sub.1 -C.sub.3 haloalkyl or --S(O).sub.n C.sub.1 -C.sub.3 alkyl groups and which may additionally be substituted by one or more chlorine atom.
South African patent application No. 84/2722 discloses, in part, herbicidal sulfonamides of formula ##STR6## wherein A is a radical of the formula CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;